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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:43 UTC

Update Date

2022-03-07 02:53:31 UTC

HMDB ID

HMDB0032928

Secondary Accession Numbers

HMDB32928

Metabolite Identification

Common Name

2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline

Description

2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline belongs to the class of organic compounds known as quinoxalines. Quinoxalines are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring. Based on a literature review a significant number of articles have been published on 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0032928
     RDKit          3D
2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline
 30 32  0  0  0  0  0  0  0  0999 V2000
    4.5553    1.7909   -0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5187    0.7502   -0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8568   -0.5578   -0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8633   -1.4504    0.1037 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5500   -1.0951    0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5337   -2.0055    0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8122   -1.6322    0.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8975   -2.6124    0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1068   -0.3071    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0807    0.6354   -0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6934    1.8077   -0.3341 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0145    1.6831   -0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9664    2.7222   -0.4222 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2714    0.3581   -0.0527 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5872   -0.1982    0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2261    0.2217   -0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2129    1.1059   -0.2984 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1005    2.7800   -0.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1190    1.5087   -1.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2218    1.8682    0.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8941   -0.9013   -0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7523   -3.0487    0.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111   -3.6307    0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6878   -2.5924   -0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633   -2.6429    1.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9008    2.5972   -0.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7366    3.6798   -0.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7421   -0.8587    0.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284   -0.6365   -0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3045    0.6606    0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  2  0
 17  2  1  0
 16  5  1  0
 14  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
 13 26  1  0
 13 27  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
M  END


  Mrv0541 02241215352D          

 17 19  0  0  0  0            999 V2000
   -1.0519   -0.2429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2422   -0.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3235   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1333   -0.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0235   -1.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2952   -1.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6474   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0802   -1.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280   -1.8616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4564   -1.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183   -0.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4281   -0.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4281    0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6191    0.4041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3235    0.8094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1333    1.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3758    1.8616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 11  2  0  0  0  0
  2  3  1  0  0  0  0
  2  8  2  0  0  0  0
  3  4  2  0  0  0  0
  3 15  1  0  0  0  0
  4  6  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 16  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032928

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(N)=NC2=C1C(C)=CC1=C2N=C(C)C=N1

> <INCHI_IDENTIFIER>
InChI=1S/C12H13N5/c1-6-4-8-9(15-7(2)5-14-8)10-11(6)17(3)12(13)16-10/h4-5H,1-3H3,(H2,13,16)

> <INCHI_KEY>
LAZSIJHHPMHKQI-UHFFFAOYSA-N

> <FORMULA>
C12H13N5

> <MOLECULAR_WEIGHT>
227.2651

> <EXACT_MASS>
227.117095441

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
25.017885679259145

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxalin-2-amine

> <ALOGPS_LOGP>
1.35

> <JCHEM_LOGP>
1.309128228

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.138759353271001

> <JCHEM_POLAR_SURFACE_AREA>
69.62

> <JCHEM_REFRACTIVITY>
65.06400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,8-trimethylimidazo[4,5-f]quinoxalin-2-amine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032928
     RDKit          3D
2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline
 30 32  0  0  0  0  0  0  0  0999 V2000
    4.5553    1.7909   -0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5187    0.7502   -0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8568   -0.5578   -0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8633   -1.4504    0.1037 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5500   -1.0951    0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5337   -2.0055    0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8122   -1.6322    0.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8975   -2.6124    0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1068   -0.3071    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0807    0.6354   -0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6934    1.8077   -0.3341 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0145    1.6831   -0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9664    2.7222   -0.4222 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2714    0.3581   -0.0527 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5872   -0.1982    0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2261    0.2217   -0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2129    1.1059   -0.2984 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1005    2.7800   -0.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1190    1.5087   -1.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2218    1.8682    0.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8941   -0.9013   -0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7523   -3.0487    0.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111   -3.6307    0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6878   -2.5924   -0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633   -2.6429    1.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9008    2.5972   -0.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7366    3.6798   -0.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7421   -0.8587    0.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284   -0.6365   -0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3045    0.6606    0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  2  0
 17  2  1  0
 16  5  1  0
 14  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
 13 26  1  0
 13 27  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      -1.963  -0.453   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -0.452  -0.906   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.604  -0.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.115  -0.453   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.777  -2.418   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.418  -1.963   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.209  -2.870   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.150  -2.418   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.359  -3.475   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -2.719  -3.021   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.021  -1.511   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.532  -1.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.532   0.754   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.022   0.754   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       0.604   1.511   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.115   1.963   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.568   3.475   0.000  0.00  0.00           N+0
CONECT    1    2   11                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    6   14                                                  
CONECT    5    6                                                            
CONECT    6    4    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    2    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    1   10   12                                                  
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14    4   13   16                                                  
CONECT   15    3   16                                                       
CONECT   16   14   15   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0032928
HETATM    1  C1  UNL     1       4.555   1.791  -0.475  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.519   0.750  -0.276  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.857  -0.558  -0.070  1.00  0.00           C  
HETATM    4  N1  UNL     1       2.863  -1.450   0.104  1.00  0.00           N  
HETATM    5  C4  UNL     1       1.550  -1.095   0.081  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.534  -2.005   0.259  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.812  -1.632   0.234  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.898  -2.612   0.424  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.107  -0.307   0.025  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.081   0.635  -0.158  1.00  0.00           C  
HETATM   11  N2  UNL     1      -0.693   1.808  -0.334  1.00  0.00           N  
HETATM   12  C10 UNL     1      -2.015   1.683  -0.277  1.00  0.00           C  
HETATM   13  N3  UNL     1      -2.966   2.722  -0.422  1.00  0.00           N  
HETATM   14  N4  UNL     1      -2.271   0.358  -0.053  1.00  0.00           N  
HETATM   15  C11 UNL     1      -3.587  -0.198   0.075  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.226   0.222  -0.126  1.00  0.00           C  
HETATM   17  N5  UNL     1       2.213   1.106  -0.298  1.00  0.00           N  
HETATM   18  H1  UNL     1       4.101   2.780  -0.624  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.119   1.509  -1.400  1.00  0.00           H  
HETATM   20  H3  UNL     1       5.222   1.868   0.404  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.894  -0.901  -0.042  1.00  0.00           H  
HETATM   22  H5  UNL     1       0.752  -3.049   0.424  1.00  0.00           H  
HETATM   23  H6  UNL     1      -1.411  -3.631   0.302  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.688  -2.592  -0.324  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.263  -2.643   1.480  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.901   2.597  -0.858  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.737   3.680  -0.078  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.742  -0.859   0.936  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.928  -0.636  -0.886  1.00  0.00           H  
HETATM   30  H13 UNL     1      -4.304   0.661   0.251  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   17
CONECT    3    4   21
CONECT    4    5    5
CONECT    5    6   16
CONECT    6    7    7   22
CONECT    7    8    9
CONECT    8   23   24   25
CONECT    9   10   10   14
CONECT   10   11   16
CONECT   11   12   12
CONECT   12   13   14
CONECT   13   26   27
CONECT   14   15
CONECT   15   28   29   30
CONECT   16   17   17
END

HMDB0032928
     RDKit          3D
2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline
 30 32  0  0  0  0  0  0  0  0999 V2000
    4.5553    1.7909   -0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5187    0.7502   -0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8568   -0.5578   -0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8633   -1.4504    0.1037 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5500   -1.0951    0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5337   -2.0055    0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8122   -1.6322    0.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8975   -2.6124    0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1068   -0.3071    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0807    0.6354   -0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6934    1.8077   -0.3341 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0145    1.6831   -0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9664    2.7222   -0.4222 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2714    0.3581   -0.0527 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5872   -0.1982    0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2261    0.2217   -0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2129    1.1059   -0.2984 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1005    2.7800   -0.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1190    1.5087   -1.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2218    1.8682    0.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8941   -0.9013   -0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7523   -3.0487    0.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111   -3.6307    0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6878   -2.5924   -0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633   -2.6429    1.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9008    2.5972   -0.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7366    3.6798   -0.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7421   -0.8587    0.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284   -0.6365   -0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3045    0.6606    0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  2  0
 17  2  1  0
 16  5  1  0
 14  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
 13 26  1  0
 13 27  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-amino-3,4,8-trimethylimidazo(4,5-F)Quinoxaline	HMDB, MeSH
2-amino-3,4,8-trimethylimidazo[4,5-F ]Quinoxaline	HMDB
3,4,8-Trimethyl-3H-imidazo(4,5-F)quinoxalin-2-amine	HMDB
3,4,8-Trimethyl-3H-imidazo[4,5-F]quinoxalin-2-amine, 9ci	HMDB
3,4,8-trimethylimidazo(4,5-F)Quinoxalin-2-amine	HMDB, MeSH
4,8-Di-meiqx	HMDB
4,8-Dimethyl iqx	HMDB
4,8-Dimethyl-iqx	HMDB
Di-meiqx	HMDB
Dimethyl-iqx	HMDB
3,4,8-MeIQX	MeSH, HMDB
4,8-DiMeIQx	MeSH, HMDB

Chemical Formula

C₁₂H₁₃N₅

Average Molecular Weight

227.2651

Monoisotopic Molecular Weight

227.117095441

IUPAC Name

3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxalin-2-amine

Traditional Name

3,4,8-trimethylimidazo[4,5-f]quinoxalin-2-amine

CAS Registry Number

95896-78-9

SMILES

CN1C(N)=NC2=C1C(C)=CC1=C2N=C(C)C=N1

InChI Identifier

InChI=1S/C12H13N5/c1-6-4-8-9(15-7(2)5-14-8)10-11(6)17(3)12(13)16-10/h4-5H,1-3H3,(H2,13,16)

InChI Key

LAZSIJHHPMHKQI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinoxalines. Quinoxalines are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinoxalines

Alternative Parents

Substituents

Quinoxaline
Benzimidazole
Aminoimidazole
Benzenoid
Pyrazine
N-substituted imidazole
Azole
Heteroaromatic compound
Imidazole
Azacycle
Primary amine
Amine
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032928)
Cytoplasm (HMDB: HMDB0032928)

Source

Exogenous

Exogenous (HMDB: HMDB0032928)

Food

Food (HMDB: HMDB0032928)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032928)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	300 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.43 g/L	ALOGPS
logP	1.35	ALOGPS
logP	1.31	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	5.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.62 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	65.06 m³·mol⁻¹	ChemAxon
Polarizability	25.02 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	150.985	31661259
DarkChem	[M-H]-	153.099	31661259
DeepCCS	[M+H]+	154.795	30932474
DeepCCS	[M-H]-	152.399	30932474
DeepCCS	[M-2H]-	185.441	30932474
DeepCCS	[M+Na]+	160.736	30932474
AllCCS	[M+H]+	151.1	32859911
AllCCS	[M+H-H2O]+	147.1	32859911
AllCCS	[M+NH4]+	154.8	32859911
AllCCS	[M+Na]+	155.9	32859911
AllCCS	[M-H]-	155.7	32859911
AllCCS	[M+Na-2H]-	155.5	32859911
AllCCS	[M+HCOO]-	155.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	2.33 minutes	32390414
Predicted by Siyang on May 30, 2022	9.6967 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.14 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	86.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	829.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	247.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	91.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	156.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	51.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	320.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	296.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	668.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	635.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	40.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	834.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	152.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	211.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	621.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	493.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	303.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline	CN1C(N)=NC2=C1C(C)=CC1=C2N=C(C)C=N1	2977.5	Standard polar	33892256
2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline	CN1C(N)=NC2=C1C(C)=CC1=C2N=C(C)C=N1	2338.1	Standard non polar	33892256
2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline	CN1C(N)=NC2=C1C(C)=CC1=C2N=C(C)C=N1	2612.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline,1TMS,isomer #1	CC1=CN=C2C=C(C)C3=C(N=C(N[Si](C)(C)C)N3C)C2=N1	2631.2	Semi standard non polar	33892256
2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline,1TMS,isomer #1	CC1=CN=C2C=C(C)C3=C(N=C(N[Si](C)(C)C)N3C)C2=N1	2314.7	Standard non polar	33892256
2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline,2TMS,isomer #1	CC1=CN=C2C=C(C)C3=C(N=C(N([Si](C)(C)C)[Si](C)(C)C)N3C)C2=N1	2508.9	Semi standard non polar	33892256
2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline,2TMS,isomer #1	CC1=CN=C2C=C(C)C3=C(N=C(N([Si](C)(C)C)[Si](C)(C)C)N3C)C2=N1	2402.3	Standard non polar	33892256
2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline,1TBDMS,isomer #1	CC1=CN=C2C=C(C)C3=C(N=C(N[Si](C)(C)C(C)(C)C)N3C)C2=N1	2832.6	Semi standard non polar	33892256
2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline,1TBDMS,isomer #1	CC1=CN=C2C=C(C)C3=C(N=C(N[Si](C)(C)C(C)(C)C)N3C)C2=N1	2482.3	Standard non polar	33892256
2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline,2TBDMS,isomer #1	CC1=CN=C2C=C(C)C3=C(N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N3C)C2=N1	2865.0	Semi standard non polar	33892256
2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline,2TBDMS,isomer #1	CC1=CN=C2C=C(C)C3=C(N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N3C)C2=N1	2819.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0h9a-0940000000-287862590f79af87e30c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline 10V, Positive-QTOF	splash10-004i-0090000000-7abee065db4c96324989	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline 20V, Positive-QTOF	splash10-004i-0190000000-5ddf35b2e0858da7c22c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline 40V, Positive-QTOF	splash10-05am-1910000000-ff5135ab675447c758c2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline 10V, Negative-QTOF	splash10-004i-0090000000-21bed679607205f1e60a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline 20V, Negative-QTOF	splash10-004i-0190000000-213c797e2d539b492d32	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline 40V, Negative-QTOF	splash10-03dl-5590000000-dea2ecb8b10fa6387dff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline 10V, Negative-QTOF	splash10-004i-0090000000-eaa75a9a8c9828a1b313	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline 20V, Negative-QTOF	splash10-004i-0390000000-51dde21eb5f0e0f76453	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline 40V, Negative-QTOF	splash10-05fs-0900000000-155b8adfd1cb3b5950cf	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline 10V, Positive-QTOF	splash10-004i-0090000000-7d0a9d062589b22b4faf	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline 20V, Positive-QTOF	splash10-004i-0090000000-490293f154e2cc683e9f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline 40V, Positive-QTOF	splash10-0a6s-4920000000-c9f7bda89466009a3457	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010913

KNApSAcK ID

Not Available

Chemspider ID

94552

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

104739

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Aschebrook-Kilfoy B, Ollberding NJ, Kolar C, Lawson TA, Smith SM, Weisenburger DD, Chiu BC: Meat intake and risk of non-Hodgkin lymphoma. Cancer Causes Control. 2012 Oct;23(10):1681-92. doi: 10.1007/s10552-012-0047-2. Epub 2012 Aug 14. [PubMed:22890783 ]
Guo H, Pan H, Wang Z, Chen L, Zhang D: [Simultaneous determination of nine heterocyclic aromatic amines in mutton products by solid phase extraction-high performance liquid chromatography]. Se Pu. 2012 Oct;30(10):1074-80. [PubMed:23383498 ]
Miller PE, Lazarus P, Lesko SM, Cross AJ, Sinha R, Laio J, Zhu J, Harper G, Muscat JE, Hartman TJ: Meat-related compounds and colorectal cancer risk by anatomical subsite. Nutr Cancer. 2013;65(2):202-26. doi: 10.1080/01635581.2013.756534. [PubMed:23441608 ]
Puangsombat K, Gadgil P, Houser TA, Hunt MC, Smith JS: Occurrence of heterocyclic amines in cooked meat products. Meat Sci. 2012 Mar;90(3):739-46. doi: 10.1016/j.meatsci.2011.11.005. Epub 2011 Nov 9. [PubMed:22129588 ]
Van Hemelrijck M, Rohrmann S, Steinbrecher A, Kaaks R, Teucher B, Linseisen J: Heterocyclic aromatic amine [HCA] intake and prostate cancer risk: effect modification by genetic variants. Nutr Cancer. 2012;64(5):704-13. doi: 10.1080/01635581.2012.678548. Epub 2012 May 7. [PubMed:22564066 ]
Jahurul MH, Jinap S, Ang SJ, Abdul-Hamid A, Hajeb P, Lioe HN, Zaidul IS: Dietary exposure to heterocyclic amines in high-temperature cooked meat and fish in Malaysia. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2010 Aug;27(8):1060-71. doi: 10.1080/19440041003801190. [PubMed:20589547 ]
Dundar A, Saricoban C, Yilmaz MT: Response surface optimization of effects of some processing variables on carcinogenic/mutagenic heterocyclic aromatic amine (HAA) content in cooked patties. Meat Sci. 2012 Jul;91(3):325-33. doi: 10.1016/j.meatsci.2012.02.011. Epub 2012 Feb 22. [PubMed:22405910 ]
Daniel CR, Sinha R, Park Y, Graubard BI, Hollenbeck AR, Morton LM, Cross AJ: Meat intake is not associated with risk of non-Hodgkin lymphoma in a large prospective cohort of U.S. men and women. J Nutr. 2012 Jun;142(6):1074-80. doi: 10.3945/jn.112.158113. Epub 2012 Apr 25. [PubMed:22535761 ]
Shao B, Peng Z, Yang H, Wu G, Yao Y, Wan K: [Simultaneous determination of 9 heterocyclic aromatic amine in poultry products by solid-phase extraction-high performance liquid chromatography]. Se Pu. 2011 Aug;29(8):755-61. [PubMed:22128739 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline (HMDB0032928)

MOL for HMDB0032928 (2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline)

3D MOL for HMDB0032928 (2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline)

3D SDF for HMDB0032928 (2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline)

3D-SDF for HMDB0032928 (2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline)

PDB for HMDB0032928 (2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline)

3D PDB for HMDB0032928 (2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline)

SMILES for HMDB0032928 (2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline)

INCHI for HMDB0032928 (2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline)

Structure for HMDB0032928 (2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline)

3D Structure for HMDB0032928 (2-Amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra